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LOT 4001
Al Black "Jacaranda on the Lake" Florida Highwaymen Oil Painting, 24"X18"
Est. $500-$1,000

“Jacaranda on the Lake” by Al Black is a 24” x 18” oil painting that showcases the vibrant beauty of Florida’s landscapes. As a Florida Highwaymen artist, Al Black brings this serene lakeside scene to life with bold colors and expressive brushstrokes. The jacaranda trees add a striking contrast, making this piece a standout for collectors and art lovers.




LOT 4001A
Michael Love "4 Silhouettes" 2nd Generation Florida Highwaymen Silhouette Paintings
Est. $200-$600

“4 Silhouettes” by Michael Love is a striking piece that embodies the essence of the Florida Highwaymen’s legacy. As a 2nd Generation Highwaymen artist, Love masterfully captures the beauty of Florida’s landscapes through the distinct use of silhouetted figures set against a luminous backdrop. This painting showcases his refined technique and deep appreciation for the bold, atmospheric style pioneered by the original Highwaymen. A must-have for collectors seeking a contemporary yet timeless tribute to Florida’s artistic heritage.

LOT 4002
R.L. Lewis "Postcard Jacaranda" Florida Highwaymen Canvas Panel Oil Painting 5"X7"
Est. $500-$1,000

“Postcard Jacaranda” by R.L. Lewis is a captivating 5” x 7” oil painting on canvas panel that beautifully reflects the timeless charm of Florida’s landscapes. As an esteemed Florida Highwaymen artist, Lewis skillfully portrays the iconic jacaranda tree in full bloom, using rich hues and expressive brushwork to evoke a sense of nostalgia and natural beauty. Despite its compact size, this piece carries the signature vibrancy and movement that define the Highwaymen style, making it a perfect addition for collectors and admirers of Florida’s artistic heritage.

LOT 4003
Al Black "Eddie's Place" 24X36 Masonite, Florida Highwaymen Painting
Est. $500-$1,000

“Small Back Water” by James Gibson is an 18” x 12” Masonite oil painting that captures the tranquil beauty of Florida’s hidden waterways. A masterful work by a Florida Highwaymen artist, this piece features rich, atmospheric colors and detailed brushwork, bringing to life the stillness and serenity of a secluded backwater scene. A timeless addition for collectors and admirers of Florida’s natural landscapes.

LOT 4004
Jimmy Stoval "Green Bay" Florida Landscape Masonite Painting 12"X24"
Est. $500-$1,000

“Green Bay” by Jimmy Stovall is a 12” x 24”
Masonite painting that beautifully portrays Florida’s lush, untouched landscapes. As a Florida Highwaymen artist, Stovall uses rich greens and dynamic brushstrokes to capture the natural vibrancy of the bay. This striking piece reflects the timeless beauty of Florida’s waterways, making it a perfect addition for collectors and nature enthusiasts.

LOT 4005
R.A. Mclendon "Purple and Yellow Tree on the Lake" Florida Highwaymen Canvas Oil Painting, 18"X24"
Est. $3,500-$5,500

“Purple and Yellow Tree on the Lake” by R.A. McLendon is an 18” x 24” oil painting on canvas that showcases the vivid beauty of Florida’s natural scenery. As a distinguished Florida Highwaymen artist, McLendon masterfully blends bold purples, yellows, and deep blues to depict a peaceful lakeside view. His expressive brushwork and use of vibrant colors make this piece a captivating addition for collectors and admirers of Florida’s iconic landscapes.

LOT 4006
Robert Butler, Multi-artist, Florida Highwaymen Oil Painting (many artists) 16"X20"
Est. $2,500-$5,000

This 16” x 20” Florida Highwaymen oil painting is a rare multi-artist collaboration featuring the work of Robert Butler and other renowned Highwaymen painters. Showcasing a harmonious blend of styles, this piece beautifully captures Florida’s diverse landscapes with rich colors and expressive brushstrokes. A unique and highly collectible artwork, it represents the shared vision and legacy of the iconic Highwaymen movement.



LOT 4007
RA Mclendon "Small Rio Mar" Florida Highwaymen Canvas Oil Painting 14"X11"
Est. $2,000-$3,400

“Small Rio Mar” by R.A. McLendon is a captivating 14” x 11” oil painting on canvas that showcases the natural beauty of Florida’s coastal landscapes. As a distinguished Florida Highwaymen artist, McLendon expertly blends bold brushstrokes and a vibrant color palette to depict the peaceful shoreline. The shimmering water and lush surroundings evoke a sense of serenity, making this piece a testament to his signature style. A timeless addition for collectors and admirers of classic Florida Highwaymen art.

LOT 4007A
Tracy Newton "Rainbow Fire Sky" 2nd Generation Florida Highwaymen Canvas Oil Painting 16"X20"
Est. $400-$800

“Rainbow Fire Sky” by Tracy Newton is a mesmerizing 16” x 20” oil painting on canvas that captures the breathtaking drama of a Florida sunset. As a 2nd Generation Florida Highwaymen artist, Newton masterfully blends bold, radiant hues to create a sky ablaze with color, reflecting the untamed beauty of the Sunshine State. His signature brushwork and dynamic composition bring the scene to life, making this piece a stunning tribute to the Highwaymen legacy. A must-have for collectors who appreciate vivid, atmospheric landscapes.

LOT 4008
Al Black 'Perfect Day on the Beach" Florida Highwaymen Canvas Oil Painting 24"X30"
Est. $750-$1,500

“Perfect Day on the Beach” by Al Black is a 24” x 30” oil painting on canvas that captures the essence of Florida’s serene coastline. As a celebrated Florida Highwaymen artist, Black uses bold colors and expressive brushstrokes to depict a sunlit beach scene with rolling waves and a tranquil atmosphere. This vibrant piece is a stunning tribute to Florida’s natural beauty, making it a prized addition for collectors and coastal art enthusiasts.

LOT 4009
Mary Ann Carroll "Vibrant Fire Sky Backwater" Florida Highwaymen Upson Oil Painting 24"X32"
Est. $6,000-$12,000

“Vibrant Fire Sky Backwater” by Mary Ann Carroll is a 24” x 32” oil painting on Upson board, showcasing a breathtaking Florida sunset over a secluded backwater. As the only female artist among the Florida Highwaymen, Carroll’s bold use of fiery reds, oranges, and deep purples creates a dramatic sky that reflects beautifully on the water. This striking piece embodies her signature expressive style, making it a standout addition for collectors and admirers of Florida’s iconic landscapes.

LOT 4009A
Isaac Knight "Pink and Yellow Sky" Florida Highwaymen Upson Oil Painting 18"X24"
Est. $1,200-$2,000

“Pink and Yellow Sky” by Isaac Knight is a breathtaking 18” x 24” oil painting on Upson board that captures the radiant beauty of a Florida sunset. As a revered Florida Highwaymen artist, Knight masterfully blends warm pinks and golden yellows to create a sky that glows with intensity, casting a serene light over the tranquil landscape below. His signature brushwork and rich color palette bring depth and movement to the scene, making this piece a striking addition for collectors who appreciate the timeless allure of Highwaymen artistry.

LOT 4010
Rodney Demps " Orange Backwater" Florida Highwaymen Masonite Oil Painting 24"X48"
Est. $1,000-$2,000

“Orange Backwater” by Rodney Demps is a 24” x 48” Masonite oil painting that captures the warm glow of a Florida sunset over a peaceful waterway. As a Florida Highwaymen artist, Demps uses rich oranges, deep blues, and dynamic brushstrokes to bring this serene landscape to life. The painting’s expansive size and vivid colors make it a captivating statement piece, perfect for collectors and enthusiasts of Florida’s natural beauty.

LOT 4011
Carina L. Guerra, Usko Ayar Peruvian Landscape Painting 1994 22"X27.5" Gouache paint on Arches Paper
Est. $500-$1,000

This 1994 Peruvian landscape painting by Carina L. Guerra, titled “Usko Ayar,” is a 22” x 27.5” gouache painting on Arches paper. Rich in cultural heritage and vibrant detail, the piece beautifully captures the essence of Peru’s natural scenery with bold colors and intricate brushwork. The use of gouache on high-quality Arches paper enhances the depth and texture, making it a striking and collectible artwork for admirers of South American landscapes and traditional artistry.

LOT 4012
Lister P. Ruiz, Usko Ayar Peruvian Landscape Painting 1995 15"X21" Gouache paint on Arches
Est. $500-$1,000

This 1995 Peruvian landscape painting by Lister P. Ruiz, titled “Usko Ayar,” is a 15” x 21” gouache painting on Arches paper. Showcasing the rich natural beauty of Peru, Ruiz uses vibrant colors and meticulous brushwork to bring the landscape to life. The gouache medium enhances the depth and texture, making this piece a visually captivating and collectible work for those who appreciate traditional South American artistry and cultural landscapes.

LOT 4013
Juan Amaringo - "Psychedelic Shaman" Ayahuasca Inspired Visionary Art 32"X24" Acrylic on Canvas
Est. $500-$1,500

“Psychedelic Shaman” by Juan Amaringo is a 32” x 24” acrylic painting on canvas, inspired by the mystical visions of Ayahuasca. A striking example of visionary art, this piece showcases intricate details, vibrant colors, and symbolic imagery that reflect spiritual and shamanic experiences. Amaringo, known for his deep connection to Amazonian traditions, brings a transcendent quality to his work, making this painting a mesmerizing and highly collectible piece for those drawn to sacred and psychedelic art.

LOT 4014
Willie Daniels "Red Night Sky" 20X16 Oil Paint on Canvas Board, , Florida Highwaymen Painting
Est. $1,500-$3,000

‘Red Night Sky’ by Willie Daniels features a dramatic Florida landscape under a glowing red-hued night sky. The vibrant tones of the sky reflect softly on the tranquil waters below, while shadowed palms and foliage add depth and contrast to the composition. This 20”x16” oil painting on canvas board showcases Daniels’ mastery of bold color and atmospheric detail, capturing the timeless beauty of Florida’s tropical nights in classic Highwaymen style.

LOT 4015
Johnny Daniels "Blue Lit Bay" Florida Highwaymen Masonite Oil Painting 24"X18"
Est. $2,000-$3,000

“Blue Lit Bay” by Johnny Daniels is a 24” x 18” Masonite oil painting that captures the tranquil beauty of Florida’s coastal waters under a soft blue glow. A celebrated Florida Highwaymen artist, Daniels masterfully uses cool tones and expressive brushstrokes to create a peaceful, atmospheric scene. This piece reflects his signature style and deep appreciation for Florida’s natural landscapes, making it a valuable addition for collectors and art enthusiasts.

LOT 4016
Al Black "Poinciana in Back Water" Florida Highwaymen Canvas Board Oil Painting 18X12
Est. $1,000-$2,000

“Poinciana in Back Water” by Al Black is an 18” x 12” oil painting on canvas board, showcasing the vivid beauty of Florida’s waterways framed by the striking red blooms of a Royal Poinciana tree. As a Florida Highwaymen artist, Black’s bold brushstrokes and rich color palette bring this serene backwater scene to life. A classic example of his work, this piece is a perfect addition for collectors and admirers of Florida’s natural landscapes.

LOT 4016A
C.H. Alderman, "Boat on the River" Florida Landscape Painting 19"X29"
Est. $300-$500

“Boat on the River” by C.H. Alderman is a stunning 19” x 29” Florida landscape painting that beautifully captures the peaceful allure of the state’s waterways. With a keen eye for detail and a rich, natural color palette, Alderman brings this tranquil riverside scene to life, evoking a sense of serenity and nostalgia. The gentle reflections on the water and the carefully placed boat create a harmonious composition, making this piece a perfect addition for collectors who appreciate classic Florida landscapes and masterful craftsmanship.

LOT 4017
Sam Newton, "Trifecta" Florida Highwaymen Masonite Oil Painting 16X20
Est. $8,000-$20,000

“Trifecta” by Sam Newton is a 16” x 20” Masonite oil painting that captures the timeless beauty of Florida’s landscapes with rich colors and masterful composition. As a renowned Florida Highwaymen artist, Newton’s work is known for its serene atmospheres and breathtaking natural scenery. This piece exemplifies his signature style, making it a must-have for collectors and enthusiasts of Florida’s iconic Highwaymen art.


LOT 4018
Sam Newton "Blue Sky Poinciana" Florida Highwaymen Upson Oil Painting 24"X36"
Est. $6,000-$10,000

“Blue Sky Poinciana” by Sam Newton is a breathtaking 24” x 36” oil painting on Upson board that showcases the vibrant beauty of Florida’s iconic royal poinciana tree. As a legendary Florida Highwaymen artist, Newton masterfully contrasts the tree’s fiery red blossoms against a brilliant blue sky, creating a striking composition full of depth and movement. His skilled brushwork and rich color palette capture the essence of Florida’s natural splendor, making this piece a standout addition for collectors and admirers of Highwaymen artistry.

LOT 4018A
Doretha Hair, "Vibrant Fire Sky" Florida Landscape Canvas Oil Painting 16"X20" Masonite
Est. $300-$600

“Vibrant Fire Sky” by Doretha Hair is a captivating 16” x 20” oil painting on Masonite that radiates the fiery beauty of a Florida sunset. As a renowned Florida Highwaymen artist, Hair masterfully blends deep oranges, rich reds, and golden yellows to create a sky ablaze with color, reflecting the warmth and intensity of the Sunshine State. Her fluid brushstrokes and striking contrasts bring the landscape to life, making this piece a stunning representation of the Highwaymen legacy. A must-have for collectors who appreciate bold, atmospheric Florida landscapes.

LOT 4019
Harold Newton "2 Palms" Florida Highwaymen Masonite Oil Painting 24"X18"
Est. $3,000-$6,000

“2 Palms” by Harold Newton is a stunning 24” x 18” oil painting on Masonite that embodies the timeless beauty of Florida’s tropical landscapes. As one of the original and most celebrated Florida Highwaymen artists, Newton masterfully captures the elegance of two towering palm trees set against a luminous sky, evoking a sense of tranquility and natural splendor. His signature brushwork and rich color palette bring depth and realism to the scene, making this piece a prized addition for collectors and admirers of classic Highwaymen artistry.

LOT 4019A
R.A. Mclendon, JUMBO "Boat on the River" Florida Highwaymen Upson Oil Painting 32"X40"
Est. $7,000-$10,000

“Boat on the River” by R.A. McLendon is a magnificent 32” x 40” oil painting on Upson board that captures the serene beauty of Florida’s waterways on a grand scale. As a distinguished Florida Highwaymen artist, McLendon masterfully uses bold brushstrokes and a rich color palette to bring this tranquil riverside scene to life. The peaceful flow of the water, accented by the presence of a lone boat, creates a sense of solitude and natural harmony. This JUMBO composition is a statement piece, perfect for collectors who appreciate the grandeur and timeless appeal of authentic Highwaymen artistry.

LOT 4019B
R.A. Mclendon (attributed) Unsigned "Palm on the Dock" Florida Highwaymen Upson Oil Painting 24"X36"
Est. $1,000-$2,000

“Palm on the Dock” (attributed) by R.A. McLendon is a striking 24” x 36” oil painting on Upson board that beautifully captures the essence of Florida’s coastal charm. Though unsigned, this piece reflects McLendon’s signature style, with expressive brushstrokes and a vibrant palette bringing the tranquil waters and swaying palm to life. The dock, bathed in warm light, invites the viewer into the peaceful scene, evoking the timeless allure of Florida’s waterways. A remarkable addition for collectors who appreciate the artistry and legacy of the Florida Highwaymen.

LOT 4020
James Gibson "The Single Tree" Florida Highwaymen Canvas Oil Painting 20"X16"
Est. $800-$1,600

“The Single Tree” by James Gibson is a captivating 20” x 16” oil painting on canvas that embodies the serene beauty of Florida’s landscapes. As a celebrated Florida Highwaymen artist, Gibson masterfully uses rich, atmospheric colors and fluid brushstrokes to highlight the solitary tree standing against a vibrant sky. The contrast between the tree’s graceful silhouette and the glowing backdrop creates a striking composition, evoking both tranquility and strength. A timeless piece, perfect for collectors who appreciate the elegance and nostalgia of Highwaymen artistry.

LOT 4021
R.L. Lewis "Fire Sky Backwater" Florida Highwaymen 24X36 Canvas Board Painting
Est. $2,500-$5,000

“Fire Sky Backwater” by R.L. Lewis is a 24” x 36” oil painting on canvas board that captures the dramatic beauty of a fiery Florida sunset over a secluded waterway. As a renowned Florida Highwaymen artist, Lewis uses bold reds, oranges, and deep purples to create a breathtaking sky that reflects across the tranquil waters. His signature brushwork and vibrant color palette make this piece a stunning and collectible addition for Highwaymen art enthusiasts and lovers of Florida’s landscapes.

LOT 4022
Willie Daniels, "Royal Poinciana" Florida Highwaymen Canvas Oil Painting 20"X16"
Est. $2,400-$4,000

“Royal Poinciana” by Willie Daniels is a 20” x 16” oil painting on canvas that beautifully showcases Florida’s iconic flame-colored tree in full bloom. As a skilled Florida Highwaymen artist, Daniels uses rich reds, vibrant greens, and expressive brushstrokes to bring this striking landscape to life. His attention to detail and masterful use of color make this piece a standout addition for collectors and admirers of Florida’s natural beauty.

LOT 4023
James Gibson, 'Tequila Sunrise', Highway Men - Oil Painting on Upson, 30"x24"
Est. $300-$800

“Alebrije ‘Polar Bear’” by G. Calvo is a 6” x 2” hand-carved wooden sculpture, intricately painted with oil to showcase vibrant patterns and fine details. Inspired by traditional Mexican folk art, this unique alebrije blends the mystical essence of these fantastical creatures with the strength and elegance of a polar bear. A beautifully crafted collectible, it embodies both cultural heritage and artistic creativity.

LOT 4024
E. Gonzalez - Alebrije - "Blue Stingray" - Oil Paint on Wooden Sculpture 11"X6"
Est. $300-$800

“Alebrije ‘Blue Stingray’” by E. Gonzalez is an 11” x 6” hand-carved wooden sculpture, intricately painted with oil to showcase vibrant patterns and flowing designs. Inspired by traditional Mexican folk art, this unique alebrije blends marine elegance with imaginative detailing, bringing the stingray to life in a striking fusion of color and craftsmanship. A captivating collectible, perfect for lovers of folk art and ocean-inspired creations.

LOT 4025
Mary Ann Carroll Giclee "Blue Waters" Florida Highwaymen Giclee 12"X16"
Est. $200-$500

“Blue Waters” by Mary Ann Carroll is a 12” x 16” giclee print that captures the serene beauty of Florida’s waterways with rich blues and expressive brushstrokes. As the only female Florida Highwaymen artist, Carroll’s work is known for its vibrant color palettes and masterful compositions. This high-quality giclee reproduction preserves the depth and detail of the original, making it a stunning and collectible piece for admirers of Highwaymen art and Florida’s natural landscapes.

LOT 4026
Emmit Fritz "3 Mud Paintings" Florida Landscape Mud Paintings 14"X17", 14"X16",13"X16"
Est. $600-$1,400

“3 Mud Paintings” by Emmett Fritz are a unique set of Florida landscape artworks, measuring 14” x 17”, 14” x 16”, and 13” x 16”. Created using natural earth pigments, these paintings reflect Fritz’s distinctive approach to capturing Florida’s scenic beauty with rich textures and organic tones. Each piece showcases his masterful composition and deep appreciation for the state’s landscapes, making this collection a rare and valuable addition for collectors of Florida art and natural media techniques.

LOT 4027
R.A. Mclendon, "Fire Sky Backwater" Florida Highwaymen Upson Oil Painting 24"X36"
Est. $4,000-$8,000

“Fire Sky Backwater” by R.A. McLendon is a 24” x 36” oil painting on Upson board, capturing the dramatic beauty of a fiery Florida sunset over a tranquil backwater. As a renowned Florida Highwaymen artist, McLendon’s bold use of reds, oranges, and deep purples creates a breathtaking sky that reflects across the still waters. His signature expressive brushwork and rich color palette make this piece a stunning and highly collectible artwork for lovers of Florida’s natural landscapes and Highwaymen art.

LOT 4028
Willie Daniels "Fire Sky Tall Birds" Florida Highwaymen Canvas Board Oil Painting 20"X16"
Est. $1,500-$3,000

“Fire Sky Tall Birds” by Willie Daniels is a 20” x 16” oil painting on canvas board that captures the breathtaking beauty of a Florida sunset with vivid reds, oranges, and deep purples. As a renowned Florida Highwaymen artist, Daniels brings this dynamic scene to life with his signature expressive brushstrokes, featuring graceful wading birds silhouetted against the fiery sky. This striking piece is a must-have for collectors and admirers of Florida’s natural landscapes and Highwaymen art.

LOT 4029
Harold Newton, "Dark Sky Paradise" Florida Highwaymen Masonite oil Painting 24"X36"
Est. $10,000-$20,000

“Dark Sky Paradise” by Harold Newton is a breathtaking 24” x 36” oil painting on Masonite that captures the dramatic beauty of Florida’s ever-changing skies. As a pioneering Florida Highwaymen artist, Newton masterfully contrasts a moody, darkened sky with the lush paradise below, creating a scene rich in depth and emotion. His signature brushwork and expert use of light bring the landscape to life, making this piece a powerful representation of Florida’s natural splendor. A must-have for collectors who appreciate the timeless artistry of the Highwaymen legacy.

LOT 4030
Livingston Roberts, JUMBO " Back Country Pines" Florida Highwaymen Canvas Oil Painting 30"X40"
Est. $4,000-$8,000

“Back Country Pines” by Livingston Roberts is a 30” x 40” oil painting on canvas, showcasing the raw beauty of Florida’s untouched wilderness. A masterful work by the renowned Florida Highwaymen artist, this large-scale piece features towering pines set against a vast, atmospheric sky, brought to life with rich earth tones and expressive brushstrokes. Roberts’ ability to capture depth and tranquility makes this painting a prized addition for collectors and admirers of classic Highwaymen art.

LOT 4031
Johnny Daniels "Sky of Flame" Florida Highwaymen Upson Oil Painting 24"X36"
Est. $2,600-$4,000

“Sky of Flame” by Johnny Daniels is a mesmerizing 24” x 36” oil painting on Upson board that captures the intense beauty of a Florida sunset. As a revered Florida Highwaymen artist, Daniels masterfully blends fiery reds, deep oranges, and golden yellows to create a sky that seems to glow with warmth and energy. His expressive brushstrokes and rich color contrasts bring movement and depth to the scene, making this piece a standout representation of Florida’s natural splendor. A striking addition for collectors who appreciate the bold and dramatic artistry of the Highwaymen tradition.

LOT 4032
Robert Butler - Print - "Blue Dream" Florida Highwaymen Print - Frame Measures 25"X21"
Est. $100-$300

“Blue Dream” by Robert Butler is a captivating Florida Highwaymen print that beautifully showcases the artist’s signature mastery of atmospheric landscapes. Measuring 25” x 21” in its frame, this piece transports the viewer into a serene dreamscape where cool blue tones dominate the sky and water, evoking a sense of tranquility and wonder. As a renowned Highwaymen artist, Butler was known for his ability to capture the untouched beauty of Florida’s wilderness, and this print is a perfect representation of his timeless vision. A stunning addition for collectors who appreciate the elegance and depth of Highwaymen artistry.

LOT 4032A
Mark Stanford "River Road" Florida Landscape Canvas Board Oil Painting 24"X30"
Est. $500-$1,000

“River Road” by Mark Stanford is a stunning 24” x 30” oil painting on canvas board that captures the peaceful charm of Florida’s backcountry. With a masterful blend of rich earth tones and luminous sky hues, Stanford brings this winding river road to life, evoking a sense of nostalgia and tranquility. His detailed brushwork and skillful use of light create depth and movement, making this piece a captivating tribute to Florida’s natural beauty. A perfect addition for collectors who appreciate classic Florida landscapes and fine craftsmanship.

LOT 4033
Huichol Art "Beaded Deer Head" 15"X14" Peyote Inspired Art
Est. $800-$1,600

The “Beaded Deer Head” is a 15” x 14” Huichol art piece, meticulously handcrafted with vibrant beads to depict sacred peyote-inspired symbolism. Created by the indigenous Huichol people of Mexico, this artwork represents a deep spiritual connection to nature, featuring intricate patterns and vivid colors that reflect their visionary traditions. A unique and collectible piece, it embodies cultural heritage and artistic craftsmanship, making it a standout addition for folk art enthusiasts and collectors of indigenous art.

LOT 4034
Al Black, "Backwater Jungle" Florida Highwaymen Canvas Oil Painting 24"X30"
Est. $800-$1,600

“Backwater Jungle” by Al Black is a captivating 24” x 30” oil painting on canvas that transports viewers into the heart of Florida’s untamed wilderness. As a celebrated Florida Highwaymen artist, Black masterfully uses rich greens, deep blues, and bold brushstrokes to depict a lush, secluded waterway surrounded by dense tropical foliage. The interplay of light and shadow creates depth and movement, drawing the viewer into the tranquil yet mysterious landscape. A striking addition for collectors who appreciate the raw beauty and artistry of the Highwaymen legacy.

LOT 4035
Rodney Demps, "Poinciana by the Lake" Florida Highwaymen Masonite Oil Painting 24"X36"
Est. $1,000-$2,000

“Poinciana by the Lake” by Rodney Demps is a breathtaking 24” x 36” oil painting on Masonite that beautifully captures the essence of Florida’s natural splendor. As a skilled Florida Highwaymen artist, Demps masterfully portrays the striking royal poinciana tree in full bloom, its vivid red blossoms contrasting against the tranquil lake and expansive sky. His expressive brushstrokes and rich color palette bring depth and vibrancy to the scene, making this piece a stunning tribute to Florida’s iconic landscapes. A perfect addition for collectors who appreciate the timeless beauty of Highwaymen artistry.

LOT 4037
Carnell Smith "Black Sky' Florida Highwaymen Masonite Oil Painting 24"X36"
Est. $1,500-$3,000

“Black Sky” by Carnell Smith is a 24” x 36” Masonite oil painting that captures the dramatic beauty of Florida’s landscape under a dark, moody sky. As a Florida Highwaymen artist, Smith masterfully contrasts deep blacks and grays with warm, glowing highlights, creating a striking atmosphere over the serene land and waters below. His bold brushstrokes and rich textures make this piece a captivating and collectible work, perfect for those who appreciate the artistry and legacy of the Highwaymen.

LOT 4037A
Willie Daniels, "Moonlit Bay" Florida Highwaymen Masonite Oil Painting 24"X20"
Est. $1,200-$2,000

“Moonlit Bay” by Willie Daniels is a mesmerizing 24” x 20” oil painting on Masonite that captures the serene beauty of Florida’s coastal waters under a glowing moonlit sky. As a distinguished Florida Highwaymen artist, Daniels masterfully blends soft blues, silvers, and deep shadows to create a tranquil nighttime scene where the moon’s reflection dances across the bay. His signature brushwork and atmospheric lighting add depth and realism, drawing the viewer into the peaceful solitude of the moment. A striking addition for collectors who appreciate the elegance and nostalgia of classic Highwaymen artistry.

LOT 4038
George Buckner, "The Perfect Poinciana" Florida Highwaymen Canvas Oil Painting 16"X20"
Est. $6,000-$10,000

“The Perfect Poinciana” by George Buckner is a 16” x 20” oil painting on canvas, showcasing the vibrant beauty of Florida’s iconic Royal Poinciana tree. As a talented Florida Highwaymen artist, Buckner masterfully captures the tree’s fiery red blossoms against a serene landscape, using bold brushstrokes and rich colors. This stunning piece embodies the essence of Florida’s natural beauty and is a prized addition for collectors and admirers of Highwaymen art.


LOT 4038A
Lemuel Newton, "Palm on the Dock" Florida Highwaymen Upson Oil Painting 24"X30"
Est. $2,000-$3,000

“Palm on the Dock” by Lemuel Newton is a striking 24” x 30” oil painting on Upson board that beautifully captures the serene charm of Florida’s waterfront. As a talented Florida Highwaymen artist, Newton masterfully depicts a lone palm tree swaying beside a weathered dock, bathed in warm coastal light. His rich color palette and expressive brushstrokes bring depth and movement to the tranquil waters, evoking a sense of peace and nostalgia. A timeless piece, perfect for collectors who appreciate the beauty and legacy of Highwaymen artistry.

LOT 4038B
Sam Newton, "Majestic River" Florida Highwaymen Upson Oil Painting 24"X36"
Est. $3,000-$5,000

“Majestic River” by Sam Newton is a breathtaking 24” x 36” oil painting on Upson board that captures the untouched beauty of Florida’s waterways. As a legendary Florida Highwaymen artist, Newton masterfully uses vibrant hues and fluid brushstrokes to bring this tranquil river scene to life. The interplay of light reflecting off the water and the lush greenery surrounding it creates a sense of depth and serenity, transporting the viewer to a peaceful, unspoiled paradise. A must-have for collectors who appreciate the timeless elegance of Highwaymen artistry.

LOT 4039
Livingston Roberts "Retro Poinciana" Florida Highwaymen 'Linen Upson" Oil Painting 20"X33"
Est. $6,000-$12,000

“Retro Poinciana” by Livingston Roberts is a stunning 20” x 33” oil painting on Linen Upson, showcasing the bold beauty of Florida’s iconic royal poinciana tree. As a revered Florida Highwaymen artist, Roberts masterfully blends rich, vibrant reds with lush greenery and a luminous sky, creating a nostalgic yet timeless landscape. His signature brushstrokes and expert use of color bring depth and movement to the scene, capturing the essence of Florida’s natural splendor. A remarkable piece for collectors who appreciate the elegance and history of Highwaymen artistry.

LOT 4040
Mary Ann Carroll "Backwater Lilies" Florida Highwaymen Oil Painting 24"X36"
Est. $5,000-$10,000

“Backwater Lilies” by Mary Ann Carroll is a captivating 24” x 36” oil painting that beautifully captures the tranquil essence of Florida’s hidden waterways. As the only female member of the original Florida Highwaymen, Carroll masterfully portrays a serene backwater scene, where delicate water lilies float atop still, reflective waters, framed by lush foliage and a luminous sky. Her expressive brushwork and rich color palette bring depth and vibrancy to the composition, evoking a sense of peace and nostalgia. A timeless piece, perfect for collectors who appreciate the elegance and legacy of Highwaymen artistry.

LOT 4041
Livingston Roberts, (Unsigned)"Night Palms" Florida Highwaymen Upson Oil Painting 12"X24" Each
Est. $1,000-$3,000

“Night Palms” (Unsigned) by Livingston Roberts is a stunning diptych, each panel measuring each at 12” x 24”, painted on Upson board. This rare two-piece set showcases Roberts’ signature mastery of atmospheric landscapes, capturing a moonlit Florida waterway framed by swaying palm trees and cascading Spanish moss. The deep green and blue tones create a mysterious, dreamlike quality, while the soft glow of light reflecting off the water adds depth and serenity. Encased in rustic wooden frames, this pair is a remarkable find for collectors who appreciate the timeless beauty of Highwaymen artistry.

LOT 4041A
Vernon Tynes, "Manatee and Poinciana Gator" 2nd Generation Florida Highwaymen Silhouette Painting
Est. $300-$600

“Manatee and Poinciana Gator” by Vernon Tynes is a striking silhouette painting that embodies the essence of Florida’s diverse wildlife and natural beauty. As a 2nd Generation Florida Highwaymen artist, Tynes masterfully contrasts dark silhouettes of a majestic manatee and a poised alligator against a vibrant backdrop featuring the iconic poinciana tree. His skillful use of light and shadow creates a captivating composition, evoking the timeless storytelling style of the Highwaymen tradition. A must-have for collectors who appreciate the fusion of Florida’s wildlife and artistic heritage.

LOT 4042
Willie Daniels, "Stormy Purple Rio" Florida Highwaymen Canvas Oil Painting 24"X30"
Est. $2,000-$4,000

“Stormy Purple Rio” by Willie Daniels is a breathtaking 24” x 30” oil painting on canvas that captures the raw beauty of an approaching storm over Florida’s waterways. As a renowned Florida Highwaymen artist, Daniels masterfully blends deep purples, stormy grays, and soft golden highlights to create a dramatic yet serene atmosphere. The movement of the clouds, the reflection on the water, and the contrast of light and shadow bring a sense of depth and intensity to the scene. A striking addition for collectors who appreciate the bold, atmospheric artistry of the Highwaymen legacy.

LOT 4043
Livingston Roberts, "Cotton Candy Skies" Florida Highwaymen Upson Oil Painting 24"X36"
Est. $3,000-$5,000

“Cotton Candy Skies” by Livingston Roberts is a stunning 24” x 36” oil painting on Upson board that beautifully captures the dreamy hues of a Florida sunset. As a revered Florida Highwaymen artist, Roberts masterfully blends soft pinks, purples, and warm oranges to create a sky reminiscent of delicate cotton candy, casting a tranquil glow over the serene landscape below. His signature brushstrokes bring depth and movement to the scene, evoking a sense of peace and nostalgia. A remarkable piece for collectors who appreciate the timeless beauty and artistry of the Highwaymen legacy.

LOT 4044
Robert Butler "5 Prints" Florida Highwaymen Prints 15"X16, 14"X16, 12"X16"
Est. $300-$400

“5 Prints” by Robert Butler is a stunning collection of Florida Highwaymen prints, featuring a range of serene and atmospheric landscapes that showcase Butler’s signature artistry. Measuring 15” x 16”, 14” x 16”, and 12” x 16”, each print captures the untouched beauty of Florida’s wilderness, from misty wetlands to vibrant sunsets. As a celebrated Highwaymen artist, Butler was known for his masterful use of light, rich color palettes, and detailed compositions that bring the natural world to life. This set is a perfect addition for collectors who appreciate the elegance and storytelling of Butler’s timeless work.

LOT 4045
Hezekiah Baker, "Majestic Backwater Pine" Florida Highwaymen Upson Oil Painting 24"X35.5"
Est. $2,000-$4,000

“Majestic Backwater Pine” by Hezekiah Baker is a breathtaking 24” x 35.5” oil painting on Upson board that captures the quiet grandeur of Florida’s untouched landscapes. As a skilled Florida Highwaymen artist, Baker masterfully portrays a towering pine standing proudly along a secluded backwater, bathed in the warm glow of a serene sky. His expressive brushstrokes and rich color palette bring depth and movement to the scene, evoking a sense of tranquility and nostalgia. A striking addition for collectors who appreciate the beauty and legacy of Highwaymen artistry.